UK passport holder is eligible for visa-exempt entry (without a real visa, entering for free. NOT Visa On Arrival), and will be stamped for 30 days upon entry. From his itinerary, each stay is far shorter than 30 days, and it is his first trip to Thailand after long years, he wouldn't have a problem entering Thailand on visa-exempt each time.
Having 3-proof-of (onward travel ticket, accommodation, funds of
*****
thb cash) might be good especially for 2nd entry, just in case. Not-so-frequent traveler is rarely asked for though.